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Chapter 8: 8-5 (page 225)

What product would you expect from the reaction of cyclopentene with NBS and water? Show the stereochemistry.

Short Answer

Expert verified

The product formed by the reaction of cyclopentene with NBS and water is,

Step by step solution

01

Bromohydrins from alkenes

Bromohydrins formation takes place in the presence of an NBS reagent known as N-bromosuccinimide. It is stable and easily handled, and it slowly gets decomposed in water to give .In bromohydrin formation, a bromonium ion intermediate is formed.

02

The product expected from the reaction of cyclopentene with NBS and water

The formation of bromohydrin takes place when the solvent used is DMSO and the reagent used is NBS.

When cyclopentene is reacted with NBS and water, it forms bromohydrin, where Br and OH groups are trans to each other.

Product formation

The stereochemistry of the product is,

Stereochemistry of the product.

There is an anti addition where an OH is present below the plane and Br is present above the plane.

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Most popular questions from this chapter

Question:The addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures of the carbocation intermediate to explain why none of the alternate regioisomers isformed.

Question: Which of the following alcohols could notbe made selectively by hydroboration–oxidation of an alkene? Explain.

One problem with elimination reactions is that mixtures of products are often formed. For example, treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products. What are their likely structures?

Which of the reactions below would result in a product mixture thatwould rotate plane-polarized light?

c)

Iodine azide, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene isused, only one product results:

a) Add lone-pair electrons to the structure shown for, and draw a

second resonance form for the molecule.
See all solutions

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